Pineapple Upside-down Cake Recipe

Preheat and prepare pan

Preheat oven to 350°F (175°C). Lightly grease a 9-inch round cake pan with 1 tablespoon of the unsalted butter. Place a round of parchment in the bottom if desired and grease the parchment.

Make pineapple topping base

In a small saucepan over medium heat, melt 2 tablespoons of unsalted butter with 3 tablespoons light brown sugar, stirring until sugar dissolves and mixture is slightly bubbly (about 2 minutes). Remove from heat and spoon the caramel evenly into the prepared pan, spreading to cover the bottom.

Arrange fruit

Arrange pineapple rings in a single layer over the caramel in the pan. Place a maraschino cherry in the center of each ring. If using fresh pineapple, pat rings dry first and slightly overlap where needed to fit.

Combine dry ingredients

In a large bowl, whisk together 1 1/2 cups all-purpose flour, 3 tablespoons granulated sugar, 1 1/2 teaspoons baking powder, and 1/2 teaspoon fine salt until evenly combined.

Combine wet ingredients

In a separate bowl or large measuring cup, whisk together 1/2 cup whole milk, 1 large egg, 1 teaspoon vanilla extract, and 3 tablespoons vegetable oil until smooth.

Make the batter

Pour the wet ingredients into the dry ingredients and stir gently until just combined and no large streaks of flour remain. Do not overmix. Batter will be slightly thick; if too thick to spread, add up to 1 tablespoon additional milk.

Assemble and bake

Carefully spoon or pour the batter over the arranged pineapple rings, spreading evenly to cover the fruit. Smooth the top with a spatula. Bake in the preheated oven for 30–35 minutes, or until a toothpick inserted in the center comes out clean and the cake is golden on top.

Cool and invert

Allow the cake to cool in the pan on a wire rack for 10–15 minutes. Run a knife around the edges to loosen. Place a serving plate over the cake pan and carefully invert the cake onto the plate. Lift the pan away; if any fruit sticks, gently remove and reposition. Let cool slightly before serving.

Make coconut caramel

While the cake bakes or after it comes out, make the coconut caramel sauce. In a small saucepan over medium heat, combine 3/4 cup dark brown sugar and 2 tablespoons unsalted butter. Cook, stirring, until sugar melts and mixture begins to bubble (2–3 minutes). Carefully whisk in 1/2 cup full-fat coconut milk. Bring to a gentle simmer and cook for 3–4 minutes, stirring, until slightly thickened. Remove from heat and stir in 1/2 teaspoon vanilla extract and 1/8 teaspoon salt. Taste and adjust salt or vanilla. Cool slightly; sauce will thicken more as it cools.

Serve with cake

If desired, spoon warm coconut caramel sauce over the inverted pineapple upside-down cake slices just before serving, or pass on the side for guests to drizzle.

Whip cream

Chill a medium bowl and beaters if possible. Pour 1 cup cold heavy cream into the bowl, add 2 tablespoons powdered sugar and 1/2 teaspoon vanilla extract. Whip by hand or with an electric mixer on medium-high speed until soft peaks form (about 2–3 minutes). Do not overbeat; stop when peaks hold shape but still look glossy.

Serve

Serve a dollop of vanilla whipped cream alongside each slice of cake and drizzle with coconut caramel if using.